Third Time's The Charm
by Lady.of.Victory.Rising
Summary: Rory Gilmore has been proposed to twice on graduation days. Well, you know what they say about the third time... AU Lit oneshot.


**Title-** Third Time's The Charm  
**Author-** Kàra**  
Summary-** Rory Gilmore has been proposed to twice on graduation days. Well, you know what they say about the third time... AU Lit oneshot.

**A/N-** Yes, it is _very _AU. Jess never came to Stars Hollow. They met post-finale. Deal.

* * *

**One.**

The graduation caps flew into the air, and Rory watched hers anxiously, wanting to make sure she actually got her own personal cap back, because she really wants to keep _her_ tassel, not just _a_ tassel. Once she had located the little black mortarboard amid the mass of them lying on the grass, she slipped the tassel off of the hook on the top of the cap and stuck it in the pocket of her dress beneath her robe, which was freshly unzipped due to the stifling heat of June.

A fierce hug from her mother, then Sookie and Jackson had caught her up in an exceptionally tight group hug. Her grandmother kissed her on the cheek and she hugged her startled grandfather. Yet another hug was passed on to Luke, whom she had seen fighting back tears beside her mother. She noticed with a pang that her father hadn't even bothered to show up.

But then there was Dean. Her perfect first boyfriend, her high school sweetheart, the football hero answer to her small-town princess, her first love. In the three years they had been together, there had never been more than a few weeks where they had been anything less than blissfully in love. Her mother loved him, Luke didn't trust him (but that was just Luke being overprotective), her grandparents... tolerated him, and the entire town of Stars Hollow thought he was perfect.

Rory stood up on tiptoe to kiss him, and he bent over to meet her halfway. He smiled against her mouth. "Hey," he said softly. "You did great up there."

"Yeah?"

He smiled even more widely. "Yeah. It was a great speech."

"Thanks," she said sincerely, matching him smile for smile. Except suddenly, his smile dropped away and he looked a tad nervous. Rory didn't know it, but her smile became a little uncomfortable to mirror his tense expression.

"Rory, do you think we could take a walk? I have... I have something I wanted to talk to you about."

Before Rory could answer, Lorelai announced, "Hey, we need a picture with the diploma. Tell you what, Dean, we'll take a couple of quick ones and then Rory can meet up with you. How's that sound?"

Dean shrugged and stepped away, patiently waiting for her.

Some fifteen minutes later, she disentangled herself from her mother and the very hug-enabled Sookie, to find Dean waiting for her under one of Chilton Preparatory's many colonnaded archways. "Hi," she called brightly, quickening her pace to meet him.

"Hey," he said, looking even more tense than before.

"Is everything okay?" she asked.

Dean rolled his shoulders awkwardly. "Yeah, why wouldn't it be?"

She shrugged. "I don't know. You just seem... out of sorts..."

And then he went down on one knee, pulling forth a small gold band adorned with a small diamond. "Rory Gilmore... will you marry me?"

She stared for a long second. "Are you serious?" His hurt look told her he was. "Dean, we're eighteen! We can't! We've got ages ahead of us. Can't we just... can't we just keep dating for awhile?"

"Rory, I'm sure of this. I love you! We've been together for years, doesn't that say something?"

It did, but... well... they were eighteen. She was starting at Harvard in the fall. They had their whole lives in which to get married. Why did it have to be now?

* * *

They broke up, of course. Looking back, she knew it was just puppy love, and Dean's somewhat possessive, easily wounded ego certainly couldn't survive such a blow. But it was alright, because a year and a half later, after a second-semester transfer to Yale when Harvard proved to be less than she expected and a bit of dating around, Rory met Logan...

* * *

**Two.**

Rory's cheeks were stained pink from the sun that had beat down on her while she listened to that morning's graduation speeches (the mortarboard had done absolutely nothing to shield her delicate pale skin from the glaring rays and she had had to pinch her nose to keep herself from laughing at the incongruous thought that she should have borrowed one of Luke's baseball caps), and her rosy face felt a little achey, tender from the slight burn. She felt a little out of place at this post-graduation extravaganza her grandparents had thrown for her (well, primarily for their Yale alumni friends, but ostensibly for her), twitching nervously with the hem of her green dress. It was all forgotten quickly, though, because standing next to her was Logan Huntzberger.

"So, how does it feel to be a Yale graduate?" he asked, grinning.

She smiled. "You should know, you've already done this dance," she replied.

"Ah, but it's all about the experience of the individual," Logan said wisely. "No two people feel the experience the same way. After all, isn't that what great literature is about? Sharing the experience?"

Rory giggled, a light blush suffusing her cheeks on top of her sunburn. After two and a half years of dating, she still sometimes felt blown away by him. Every once in awhile, she would still feel almost insignificant next to him. His incredible good looks, his wealth, his intelligence, his ability to be suave and charming right over the top of even the most uncomfortable situations... It amazed her that he would want to be with her, with plain old Rory Gilmore.

They had had a whirlwind romance, starting out as casual daters, eventually progressing to boyfriend and girlfriend, and after a rough patch involving infidelity, they had managed to pull together a surprisingly strong long-distance relationship while he began to build his own internet company. She had grown so much from her time with Logan; she couldn't imagine her time at Yale without him. He was her Prince Charming and, on occasion, even her knight in shining armor. Her mother... tolerated him, Luke didn't trust him (but that was just Luke being overprotective), her grandparents loved him, and the entire town of Stars Hollow thought he was perfect.

"Hey Ace?" he asked her suddenly.

"Yes?"

"Come with me."

She obeyed, curious, and followed him up to the microphone before which her grandparents had sung a (rather embarrassing, if incredibly sweet) graduation toast to her only minutes before. He took her hand and took the microphone and tapped it annoyingly to gain everyone's attention. "If I could, I'd also like to say a few words about my girlfriend of the past three years," Logan said, and Rory flushed crimson. "You amaze me, Rory Gilmore, every day. Everything that you do, everything that you are. This past year, I realized that I don't know a lot more than I thought I knew, if that makes sense. I'm a little bit nervous. I didn't think I would be. What I'm trying to say is that... I don't know a lot. But I know that I love you... and I want to be with you... forever."

He reached into his pocket and pulled out a silver ring with the largest diamond on it she had ever seen, and all Rory could think was _'Seriously?'_

"Rory Gilmore... will you marry me?" Despite his words about being nervous, she could tell that he really was confident about her reply, and was reminded bizarrely of Mr. Darcy's first, failed proposal, during which his absolute confidence had repulsed Lizzie Bennet.

"I... wow... wow... I..." Overwhelmed, she couldn't do a thing except to grab his hand and drag him off away from all the prying eyes. She had hoped one day that maybe she and Logan could get married, but she had never guessed that he would so callously chose to propose in front of at least a hundred people she didn't know (at least this time her father was there).

Finally, out on the terrace, she managed to get her bearings back. "Logan, I can't marry you!" she exclaimed. "I mean... someday. But not now. My life is wide open now, and that used to scare me, I think, but it doesn't anymore. It's exciting. And I really want to learn to be Rory Gilmore in my own right."

* * *

She had thought that Logan would stick around. They had done long distance before, they could do it again, she'd reasoned. But apparently Logan was too much like his father, refusing to take steps backwards. He had ended things when she had refused to marry him (then).

* * *

**Three.**

She honestly hadn't expected a third cap-and-gown ritual. But, a year after her graduation from Yale, when she discovered she was still having difficulty finding a job, Rory had elected to go back to her alma mater for graduate school. Now she was tossing her cap into the air for the third (and hopefully final) time, and she was elated. She had done it. She had proved wrong all the doubting voices along the road who had said that the illegitimate child of a fallen Hartford debutante, raised in a potting shed by a single mother, could never graduate from an Ivy League school. And she had done it not once, but twice.

"Hey Rory?" Lorelai caught her attention. "Luke and I are gonna drive back to the house for the _not_ party the town's throwing you. We'll meet you there?"

"Yeah, great," Rory mumbled distractedly, searching around the back of the crowd, looking for the one face she hoped most to find.

Lorelai snorted. "Go on, find your lover-boy," she said. "I know you won't be happy until you've had him do that disgusting eating-your-face thing the two of you seem to enjoy so much."

Rory waved absentmindedly to her departing mother and stepfather, continuing to search the crowd until her eyes landed on a solitary figure, leaning against a tree far away from the majority of the people. She grinned; he had put on a suit. He had presumably left the jacket off because of the sweltering heat, but it was a rare event for Jess Mariano to dress up and she enjoyed the occasions when he would put on a suit immensely (partly because he was always so adorably uncomfortable and partly because he really looked _very_ good all cleaned up).

She squirmed her way through the milling crowd and approached Jess. He pushed himself away from the tree, smirking good-naturedly at her before catching her up in a passionate kiss. "Hey," he said once their lips had parted, while his hands still rested securely on her hips.

"Hey," she said, left breathless as always by his kisses.

Jess was Luke's nephew, and through some odd conspiracy of fate, they hadn't met until years had passed since she listed Stars Hollow as her official address. He was an author, and also did some editing work for an independent publishing house in Pennsylvania. They had met two years previously when she was in Philadelphia for a three-month summer internship at the Inquirer, and sparks had flown immediately. For approximately two weeks she had thought she hated his guts, until in the middle of one of their bizarrely intense debates over Morrissey's genius (or in his opinion, lack thereof), he had kissed her out of the blue and she realized she had confused hate with falling for him.

He kissed her again. "Hey, Rory?" he asked, and she noted an odd tone in his voice.

"Yes?" she asked, looking up at him.

"At this point, I'm going to look extremely unoriginal, and I'm kind of kicking myself here, but it seemed appropriate in a twisted kind of way..." Rory couldn't help but smile that her rambling habit seemed to have worn off on the world's most reticent man. "Anyway, what I'm trying to say is I love you. I've loved you since about five minutes after I met you."

He reached into his pocket and pulled out a small black box. Rory felt her knees go weak in a way she'd never experienced before. Jess took her hand with his free one and she looked up into his eyes which were hesitant, nervous, and vulnerable in a way she rarely saw in Jess.

"Marry me, Ror?" he asked quietly.

Rory stared at her boyfriend. He was rough around the edges- Luke's sister, his mother, had been at best an inattentive mother and at worst neglectful and emotionally abusive, and his childhood had left him scarred and fraught with abandonment issues. He was no small-town hero or a Prince Charming. Her mother claimed to hate him, Luke thought of him as a son (and was freakishly overprotective of them both), her grandmother couldn't stand him (and her grandfather pretended he couldn't, though Rory suspected they had lengthy literary discussions on the sly), and the entire town of Stars Hollow was afraid of him.

He understood her in a way that nobody else ever had, not even people who had known her for her entire life. Underneath the tough exterior there was a heart of solid gold, and the sweetest, kindest man she had met (excepting, perhaps, his uncle). He was the only person she knew who read as much as she did... probably more, actually. He loved her in a way she had never experienced before, and she loved him right back with a feeling so intense, there were times it hurt just to look at him it was so deliciously overwhelming.

All this took her only seconds to think about, and then all she could think of was how cute he looked when he was nervous and how much she didn't want him to have to be nervous anymore. She threw her free arm around his neck and kissed him, unable to do anything else at this moment when he was standing there looking like that and waiting for an answer. He pulled her close and kissed her back fiercely.

When she finally relinquished his lips, he was laughing. "I take it that's a yes?" he said.

"Of course!" she exclaimed. "Oh my god!"

He chuckled again and untangled their hands so that he could wrap both his arms around her, hugging her tightly and pressing a kiss to her temple. "I love you," he said softly in her ear.

"I love you, too," she replied.

"So my extremely unoriginal idea didn't put you off at all?" he asked after a few minutes of just standing there, holding each other.

She giggled. "Nope."

"Good. I was worried. It didn't work out so well for those other guys."

Rory shook her head and pulled back from his embrace a little so that she could look him in the eyes. "With Dean and with Logan, it wasn't right," she said seriously. "There was just this little voice in the back of my head saying 'not yet, don't close off your options yet.' I always felt like I was waiting on something else. It turns out I was waiting for you."

"Just as long as you realize this means you've got to put up with me forever," Jess said teasingly, but his eyes were serious.

She grinned. "Forever sounds just about right."

* * *

And forever was just what they had. It was far from perfect- like any couple, they had their ups and downs. But Rory never once doubted that she had made exactly the right choice.

* * *

_FIN_


End file.
